methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside
CAS No.:204918-59-2
Molecular Formula:C₃₁H₃₄O₁₄
Molecular Weight:630.603
Hs Code.:

Synonyms:methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

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Chemical Property of methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

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Technology Process of methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

There total 11 articles about methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 204918-51-4
methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside

: 204918-48-9
1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside

: 204918-59-2
methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -10 ℃;
DOI:10.1016/S0960-894X(98)00049-3

Reference yield:

: 61826-42-4
tetra-O-acetyl-D-arabinofuranose

: 204918-59-2
methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

2: 86 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0 °C

With N-iodo-succinimide; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; In dichloromethane; 1: Substitution / 2: glycosylation;
DOI:10.1021/ja993543l

Reference yield:

: (2R,3S,4S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3,4-diol

: 204918-59-2
methyl 5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 418 mg / pyridine / 0 - 20 °C

2: 89 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

3: 86 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0 °C

With pyridine; N-iodo-succinimide; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: desilylation / 3: glycosylation;
DOI:10.1021/ja993543l